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Br
* *
I * * Cl
2. Answer (3)
Electron withdrawing group increases rate for SN reactions.
3. Answer (4)
Number of stereoisomers = 2n (n = number of asymmetric carbon atoms + number of double bonds)
4. Answer (1)
Meso tartaric acid is optically inactive due to presence of plane of symmetry.
5. Answer (1)
CH3 CH3
The Fisher projection of the compound is HO H and it has R & R configuration on both
H OH
asymmetric C-atom.
6. Answer (2)
7. Answer (1)
CH3
CH3
8. Answer (1)
9. Answer (4)
: CCl2 can function as an electrophile but not as a nucleophile.
10. Answer (4)
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64 Organic Chemistry Success Magnet -Solutions (Part-II)
M S, R
N R, R
O S, R
P R, S
Q R, R
Now from the above configurations we learn that
(1) M and N are diastereomers i.e., non-mirror image stereoisomers.
(2) M and O are surely identical as their configurations are same.
(3) M and P are also enantiomers due to opposite configurations.
But M and Q are again not identical but diastereomeric.
Hence answer is (1, 2, 3).
cis trans
For rings having 10C atoms cis alkenes more stable than trans.
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Success Magnet -Solutions (Part-II) Organic Chemistry 65
19. Answer (4)
Cl
Cl Cl Cl
Cl
, , , Cl
Cl
Cl
C2H5Br
CH3 – C CNa CH3 – C C – C H2 – CH3
O O OH OH
O3 Li AlH4 ⎛ Chiral centre = 2 ⎞
CH3 – C C – CH2CH3 CH3 – C – C – C2H5 CH3 – C – C – C2H5 ⎜⎝ Stereoisomer = 4 ⎟⎠
H H
THF
R – CH = CH2 + BH3 R – CH – CH2
H B–H
H
2R – CH = CH2
NH2Cl/H2O
R – CH2 – CH2 – NH2 (R – CH2 – CH2)3B
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66 Organic Chemistry Success Magnet -Solutions (Part-II)
HBr H Br
Br
Br Br
Anti-aromatic
OH
OH
H
anti-hydroxylation
aq KOH
C2H5OH
C2H5Br (1)
alc
CH2 = CH2
(2)
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Success Magnet -Solutions (Part-II) Organic Chemistry 67
37. Answer (1)
– NO2 at ‘o’ and ‘p’ position stabilize anion
F F OH
NO2 NO2
–
+ OH
CH3 CH3
NO2 NO2
F OH
O2N – –
– CH3
NO2
+ I2 + HI .
Br2
Isomeric monobrominated product
(1 eq)
h
Br2
+
h
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68 Organic Chemistry Success Magnet -Solutions (Part-II)
Cl Cl
46. Answer (3)
O
CH3
Where R = C .
H D
48. Answer (4)
Br
–
OH
OH O O
H
H
O O
H
H + – H
Br Cl
CH3 – CH = C CH3 – CH – C – COOH
COOH
Cl Br
2 chiral carbon
2
2 =4
50. Answer (3)
4 4 2
2
2 4
2
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Success Magnet -Solutions (Part-II) Organic Chemistry 69
51. Answer (1)
CH3
18
H2O
CH3 – C – CH2 +
H3C – C – CH2 Stable carbocation
O H
OH
18
H2 O
CH3 CH3
CH3 – C – CH2OH CH3 – C – CH2OH
18
O O 18
H H H
52. Answer (1)
H H
O O
O
N less stronger than
O
N O
O
Intramolecular H-bonding.
54. Answer (1)
O OH O
C C
O + 2 O + H2O
C C
O H
OH OH
(phenolphthalein)
55. Answer (4)
56. Answer (3)
AgNO 3
R – O – R + HI R – OH + RI AgI ppt.
57. Answer (1)
Depends on electronegativity of elements and stability of conjugate pair.
58. Answer (3)
Due to presence of intramolecular H bonding in (a).
59. Answer (3)
60. Answer (3)
E1 Saytzeff oriented product.
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70 Organic Chemistry Success Magnet -Solutions (Part-II)
+
OH OH2
+
+
H
H
+
+
+ –H
OH
OH
O — Fe — O
+ FeCl3 + HCl
O
(ferric phenoxide)
or (C6H5O)3Fe
H2O
[Fe(C6H5O)3(H2O)3]Cl3
Soluble complex
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Success Magnet -Solutions (Part-II) Organic Chemistry 71
+
+H (Stabilization by aromatisation and by NO2 group)
+
+H (Non-aromatic)
+
+H (Stabilization by aromatisation )
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72 Organic Chemistry Success Magnet -Solutions (Part-II)
O CH2OH
+
H
CH3
OH
71. Answer (1)
O
O O
C – OH HO – CH2
+
C – OH HO – CH2
O O
O A
HO – CH2 O
H2SO4
CH2
HO O
OH OH OH OH
O H O N N
NaOH
CH3 CH3
H2O
Compound -1 CH2 = CH – O – CH +
CH3CHO + CH3 – C – OH
CH3 H
H
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Success Magnet -Solutions (Part-II) Organic Chemistry 73
CH3
H2O
Compound-2 CH2 = C – O – C2H5 +
CH3 – C – CH3 + C2H5OH
H
O
Both (1) & (2) gives same product.
SN2
+ O O
O O
82. Answer (4)
Cross Cannizzaro reaction
HCHO is always oxidised to HCOOH other part reduced to alcohols.
O O– CH3
Cl Cl
CH3
CH3
O
CH3 – MgI
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74 Organic Chemistry Success Magnet -Solutions (Part-II)
O
+
CH2 N N
+
CH2 N N O
–
O
O CF3CO3H
CHO
5HIO4
(CHOH)4 5HCOOH + HCHO
CH2OH
O
(No elimination at bridge head carbon)
So, (1) gives positive DNP test.
89. Answer (2)
Only acid bromide and alkyl bromide undergo hydrolysis with alkali Br attached with benzene ring is resonance
stabilize therefore it give substitution at temperature and pressure.
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Success Magnet -Solutions (Part-II) Organic Chemistry 75
90. Answer (4)
COOH
HO – CH2 – CH is most acidic so pH is low.
NH3
O .. CH3
OH CH3 CH3 OCH3
..
..
CH3 H H CH3OH
..
.. O O O
OH
..
O O O O
92. Answer (3)
CH3
CH3MgI
CH3–CH2–CH2 – C N CH3 – CH2 – CH2 C = NMgI
+
H3O
CH3
O MgBr O
H2O
CH3 – C – O – CH3 CH3 – C + Mg–Br + CH3OH
OH
CH3 CH3
(1) CH3MgBr
+
(2) H3O
OH
CH3 – C – CH3
CH3
95. Answer (3)
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76 Organic Chemistry Success Magnet -Solutions (Part-II)
CH2I CHI2
In the above reaction and formed as intermediate products hence all ,
O O
O
CH2I CHI2
and give iodoform test.
O O
97. Answer (2)
CHO CH2 O H
–
CHO COO
NO2 NO2
OH
–
Conc. H2SO4 O
Conc.
O
(Cannizaro
NO2 reaction) NO2
NO2
NO2
98. Answer (4)
99. Answer (2)
Br Br
Br2 Cl H2O OH
CH3 CH2 COOH PCl3
O O
100. Answer (2)
O O O
SOCl2 CH3OH
H – O – CH2 – C – OH Cl – CH2 – C – Cl Cl – CH2 – C – O–CH3
O
CH3 CH2 C NH CH3
It should be noted that acid will be neutralised with amine.
102. Answer (1)
O O
OH
OH
OH
+ CO2
O OH
OH
O O
Molar mass = Mg (M – 44)g
O + H2O
O
(M – 62)g
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Success Magnet -Solutions (Part-II) Organic Chemistry 77
O O O O
I2 + NaOH
–CO2 C C
iodoform reaction
Ph OH Ph CH3 Ph ONa + CHI3
-keto acid E G
O O–H OH OH
+ –
H Br
+ (H – Br) H
Br Br
O O O OH
O NOH NH2
O O O
dil.
H2SO4 OH Tautomerize
OH
O OH O
H
Since compound does not have alcoholic group hence does not give victor meyer test.
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78 Organic Chemistry Success Magnet -Solutions (Part-II)
NBS Mg
dry ether
CH3CN
H2O
In esterification higher the leaving aptitude of 'X' in R C X higher will be the rate of the reaction.
O
So, rate is highest in R C Cl .
O
114. Answer (1)
O
NH2 O H H – N – C – CH2Cl
+ Cl – C – C – Cl
H AlCl3
H
N
O or C=O
N CH2
H
115. Answer (1)
Coupling occurs prefenertially in the para position to the hydroxyl group. But it this position is blocked then
coupling occurs at ortho position.
–
OH OH O
OH O
N=N N=N H
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Success Magnet -Solutions (Part-II) Organic Chemistry 79
116. Answer (3)
NaNO2
NH2 HCl N2Cl
phenanthrene
118. Answer (1)
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80 Organic Chemistry Success Magnet -Solutions (Part-II)
O
CH3 – C – H gives iodoform (haloform) test.
123. Answer (3)
O
C3H7
SOCl2 (CH3CH2CH2)2NH LiAlH4
CH3CH2COOH CH3CH2COCl CH3 – CH2 – C – N (C3H7)3N
A B C3H7 C
N CH3 OH— N CH2 + H2O
– H2O
CH3 CH3 CH3 CH3
H H
CH3
C – NH2 + O = C – C – CH3
H3C
H CH3
H H
CH3
C – N = C – C – CH3
H3C
H CH3
H2/Pt
H
CH3 – C – N – CH2 – CH(CH3)2
CH3 H
O
COOH O COOH O
COOH O
+ O
COOH COOH
COOH COOH COOH O
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Success Magnet -Solutions (Part-II) Organic Chemistry 81
129. Answer (1)
OH
OH N
+
O + H
N H
H
OH2
N
H
N–H
CH3I AgOH
CH3 CH3
N – CH3 N I
–
I
CH3 CH3
AgOH CH3I excess
CH3 CH3
N – CH3 N
–
OH CH3
133. Answer (2)
H2O2
—N + N O
H
134. Answer (1)
O
O
C
OH
O + NH3
C NH2
C
O O
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82 Organic Chemistry Success Magnet -Solutions (Part-II)
OH OH
NO2 NO2
Conc. HNO3
Conc. H2SO4
NO2
Picric acid
OH OH
NO2 NO2
Conc. HNO3
Conc. H2SO4
OH OH
NO2
Styphnic acid
137. Answer (2)
NH2 group is ortho-paradirecting in nature but during nitration in presence of H+, anillium ion is formed which is
metadirecting in nature.
Br2/KOH HNO2
C2H5CONH2 C2H5NH2 CH3 CH2 + N2
(X) (Y) OH
Mustard oil
S C S I2/NaOH
reaction
N sp3 (localised lone pair) > N sp2 (localised lone pair) > N sp2 (delocalised lone pair)
NH2
H2N NH
IV
Resonance with two NH2 groups increases electron density on 'N' of NH
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Success Magnet -Solutions (Part-II) Organic Chemistry 83
NH
Lesser increase of electron density on = NH due to
only one resonance with one –NH2
CH3 NH2
sp2
N
–
N This LPe is not available as it is involve in aromatic Sextet.
H 'N' is bonded to sp2 C on both sides.
III
N
CH3
142. Answer (1)
O H O H
N O – N O
H–N OH N
H H
O H O H
O O
Anion (conjugate pair) stabilize by resonance.
143. Answer (1)
LiAlH4 H3O
CH3 C N CH3 CH2 NH2 CH3 CH2 NH3 .
144. Answer (2)
O
CH3
C = O + H2 N – NH2 – C – NH2
H
semi carbazide
Pyridine
O
H3C
C = N . NH – C – NH2
H
Semi carbazone
O
– NH2 of – C – NH2 does not undergo condensation due to its resonance stabilization.
O O
– C – NH2 – C = NH 2
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84 Organic Chemistry Success Magnet -Solutions (Part-II)
N–O–H N – OH
H
147. Answer (2)
NaOH react with carboxylic acid.
148. Answer (4)
3° amine cannot form amine oxide.
149. Answer (3)
Due to stability of carbocation.
150. Answer (2)
CH3
CH3 – CH2 – C – C = O + H2NCH3
H H
CH3 H
CH3 – CH2 – C – C = N – CH3
H
H2/Pt.
CH3 H H
CH3 – CH2 – C – C – N – CH3
H H
151. Answer (3)
Nylon has strongest intermolecular forces (i.e. hydrogen bonding) out of these.
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Success Magnet -Solutions (Part-II) Organic Chemistry 85
155. Answer (3)
⎛ ⎞
Amino acid are amphoteric in nature. The acidic properties are due to amino group ⎜⎜ – N H3 ⎟⎟ .
⎝ ⎠
156. Answer (1)
Alanine is NH 2 – CH – COOH
CH3
CH3 CH3
(At low pH) (At high pH) –
i.e. acidic pH NH3 – CH – COOH i.e. basic pH NH2 – CH – COO
OH – OH –
H2C CH2
+ HCHO
–
CH2
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86 Organic Chemistry Success Magnet -Solutions (Part-II)
H OH
CH2OH
CHO CHO
H OH HO H
HO H H OH
H OH HO H
H OH HO H
CH2OH Mirror CH2OH
D-(+)-glucose L-(–)-glucose
CH2OH
H O H
– D – glucopyranose
OH H
OH OH
H OH
171. Answer (2)
+ C6H12O6 C6H12O6
H
C12H12O11 + H2O invertase D(+)-glucose + D(–)-fructose
sucrose ( )D = 52.7 ( )D = –92.4°
( )D = +66.5°
invert ( )D = –19.9°
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Success Magnet -Solutions (Part-II) Organic Chemistry 87
174. Answer (3)
Stearic acid, Palmatic acid and Oleic acid are higher fatty acids. Their Na salts are used as soaps.
O C NH2 O C NH
–
OBr Br Br
–HOBr
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88 Organic Chemistry Success Magnet -Solutions (Part-II)
O H O
C N Br C N Br
–
OBr
D2O
ND2 – O C N
OH
187. Answer (4)
Denaturation of protein converts quaternary, tertiary and secondary structure to primary structure.
188. Answer (2)
Invertase for carbohydrates, urease for urea and trypsin for protein.
189. Answer (4)
pH = 1 (acidic). It accepts a proton and exist as cation – NH3 is acidic group.
190. Answer (3)
Amide linkage (– CONH2)
191. Answer (4)
CH2OH
O
H * OH
5 Chiral carbon present in –D–glucose H
* OH H *
HO * * H
H OH
192. Answer (3)
CN
+ COOH
HCN H3O
H–C=O H – C – OH
(CHOH)5
(CHOH)4 (CHOH)4
CH2OH
CH2OH CH2OH
HI
COOH
(CH2)5
CH3
Heptanoic acid
193. Answer (3)
CH2OH
C= O
CH2OH
No chiral carbon
No stereoisomers.
194. Answer (2)
Ruff degradation.
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